Prohibition and a gangster named Bass
by LadyLissaLight
Summary: The Roaring 20s. The prohibition era. Chuck Bass provides illegal alchohol to people in desperate need of cutting lose. Blair Waldorf does everything she can to avoid the bootlegger, but Chuck has his heart set on her. 1920 C/B
1. Speakeasy

Another new story idea, again a trial, so let me know what you think!

**Story: **Prohibition and a gangster named Bass

**Author: ** LadyLissaLight

**Summary**: Picture the roaring 20's. The prohibition act has just come in, and Chuck Bass, bootlegger and sometimes-gangster, has never been more popular. Except, of course, with Miss Blair Waldorf.

**A/N Blair's dress, as worn by Blair herself! Just remove the spaces. **

**http : / love and headbands. wordpress. com/ page /2 /**

Blair pushed back her sleep mask, and blinked sleepily. The sunlight streamed through the open curtains, showing that it was near the middle of the day. The lacy curtains blew in the slight breeze, and the room was warm and everything had a golden glow in the light of the sun. Blair enjoyed the comfort of her bed for a few minutes longer, before stretching languidly, and tossing back the salmon pink covers of her king sized bed. She tumbled out of bed, wearing only a slip, her brown curls askew and knotted from her sleep. Throwing on a translucent white robe, she headed for her dressing table, and ran a brush through her hair.

"Miss Blair, you're awake," in bustled her maid, nanny, and confidante Dorota, whose Polish accent caused some amusement to the household guests.

"What time is it, Dorota?" Blair asked dreamily, her mind elsewhere. She had had a lovely dream, where a dark and mysterious stranger had rescued her from drowning and they had fallen in love.

Focussing on remembering the dashing qualities of her dream-saviour, Blair missed Dorota's reply.

"Excuse me?" she asked, and Dorota smiled at her fondly.

"You have a nice dream last night, Miss Blair?" She asked, knowing her charge was prone to adventurous and romantic dreams that she often preferred to real life.

"Yes," Blair smiled, "oh he was wonderful, Dorota! Dark, and handsome..." she sighed happily. "But what did you say the time was?"

"It just past midday, Miss."

"And where is mother? And Cyrus?" Eleanor Waldorf was a fashion designer, and had recently married entertainment lawyer Cyrus Rose, Blair's step-father.

They now lived in a brownstone near Fifth Avenue, New York.

"Miss Eleanor is at new model choosing, Mr Rose is at work."

Blair smiled in satisfaction; she had the house to herself. Neglecting to put on anything more, she descended the staircase and picked up the morning paper, which was lying on a sofa. Reclining, she opened to the society pages, and smiled as she read the pieces on her best friend, Serena. The other girl was the complete opposite of Blair. Her hair was as blonde as Blair's was dark, she was tall where Blair was short, and she was tanned and golden, where Blair was pale.

It seemed last night, she had been up to her usual escapades, with many men. Blair's amusement faded when she read that Serena had been rumoured to have visited a speakeasy. She stood up rapidly, tossing the paper aside.

Blair hurried up the stairs back to her room, and ignoring Dorota's offer of help, picked out her outfit for the day. She selected a champagne coloured dress, with thin straps and many overlapping layers. She paired it with black beads, and a huge black necklace, as well as midnight gloves and a clutch to match.

"Dorota! Come and fix my hair!" she ordered impatiently.

15 minutes later, her hair arranged to perfection, Blair left the house, and hurried along 5th avenue.

At the other end, she reached a house just as grand as hers, belonging to Serena's most recent step-father, Klaus, a German banker.

Ignoring the front door, she slipped to the side, and went through the side door, which she had always gone through. This door entered into the kitchen, but the cook showed no surprise at the young lady intruding upon the household. Instead she smiled, "Miss Blair. Miss Serena is still asleep, but I'm sure she'll be happy for you to wake her."

Blair nodded quickly at the woman, and ascended the stairs to Serena's room. The blonde's face was only just visible amongst the pillows and clouds of golden hair that were everywhere.

Blair sat down on the bed, and rudely shook her friends shoulder, causing a moan of annoyance.

"What, Francesca? Go 'way..." she murmured, trying to turn to face the other way.

"It's not Francesca, Its Blair!"

The blonde shot up, removing hair from her line of vision. "B!" She yawned, "What are you doing here so early?"

"I'm here, because I happened to read the society pages this morning, and see a rumour that _you_ have been going to speakeasies!" she hissed, looking around to make sure they were unheard by any gossiping servant.

Serena laughed scornfully, but the effect was spoiled by her holding her head in pain.

"Serena! You're not... hung-over... are you? Blair whispered scandalously, and Serena's expression turned defensive.

"No! I didn't drink enough for that," she added stupidly, and Blair gasped in horror.

"Serena! I am ashamed of you. How did you get into this? I mean, I know you love parties, but so do I, and I don't go to speakeasies with gangsters, and bootleggers and the like!"

Serena sighed and flopped back down in bed, her blonde hair spilling over her pillow. "It was Nate. He... well he has this friend, who introduced him to this speakeasy in the basement of this hotel, and he said it was so exciting, like the funnest party ever!" Serena giggled, and Blair tried to ignore her friend's terrible language skills and concentrate on the problem. "But what has that got to do with you?" She questioned impatiently.

"Well, once Nate told me, I had to see for myself," Serena explained. "and so last night, Nate took me to the hotel, and introduced me to his friend. His names Chuck Bass."

"Chuck Bass!" Blair gasped. "As in the bootlegger, swindler, Chuck Bass? I heard he knows Al Capone!"

Serena shrugged, seemingly uncaring about this horrifying information. "I don't know, but he is _gorgeous_, B! He's got this dark hair, and this wicked smile. I think I'm in love!" She pretended to swoon, and Blair couldn't help but crack a smile. But she quickly grew serious again. "I don't care how good looking he is, S! You can _not_ consort with bootleggers, and you can _not_ go to speakeasies! I will not let you ruin your reputation!"

Serena rolled her eyes but obediently replied, "yes, Blair."

"Good! Now, what shall we do today? I've the house to myself, or we could go and watch mother choose her new models?"

Serena shook her head at both, "let's go to the club, Blair, please? We haven't been in so long!"

'The Club' Serena mentioned was more of an indoor country club, set high up in one of the skyscrapers, and owned by Serena's step father. Serena and Blair had spent many a day curled up on one of the couches, chatting with their friends, or gossiping about a social outcast.

Since this option seemed relatively harmless, Blair agreed. They got Serena dressed in a similar outfit to Blair's, but in orange, and hurried down the street. Serena, suffering from what Blair suspected was a hang-over (no matter how much the blonde denied it), declared she was famished and she could not wait to eat.

Blair and Serena were always treated as the most important guess of the club, and today was no different. They were showed to the table with the best view over New York, and the chef cooked everything on the menu for them.

Unfortunately, as the afternoon drew on, Nate Archibald arrived. Nate was Blair and Serena's best friend; the three had grown up together and had always been inseparable. Normally, Blair would have been happy to see him but since the prohibition, or 'Volstead' act had come in last year, Nate had been acting rather pro-alcohol, and Blair did not want her, nor Serena's reputation destroyed by having anything to do with gangsters and bootleggers like Al Capone, or Jonny Torrio.

Serena, on the other hand looked very pleased to see Nate, getting up and hugging him. He wrapped his arms around her for a second, and then came over to the sofa where the two were sitting. "Blair," he smiled in greeting, but she frowned at him.

"Nathaniel Archibald! How dare you take Serena to a speakeasy!" she exclaimed as quietly as possible.

He frowned and glanced at Serena who looked guilty, "Sorry! She read it in the society pages!" she said in her defence.

"I took Serena because she wouldn't take no for an answer, and she promised she wouldn't let anyone know, much less the society pages," he said, glaring at the blonde, who blushed.

"It's just a rumour!" she protested.

"Yes," said Blair patiently, "but in our society, a rumour is worth more than a fact. And you know that, S!"

As the day drew to a close, Nate escorted the girls back to Serena's, where Blair would spend the evening.

Eventually, both girls' eyes were drooping and they fell asleep together on Serena's bed.

Blair awoke suddenly, opening her eyes just in time to see something the colour of Serena's dress disappear around the corner. She got up quickly, and pausing to check her appearance in the mirror and tidy her hair, followed the blonde out of the house and into the streets of New York.

Blair shivered at the cool night air, as did Serena, who was several metres in front of her. Serena lead Blair through the heart of Manhattan, not stopping at any of the auspicious restaurants, or cafe's that both girls liked, instead, turning towards a giant skyscraper, and entering.

Serena stepped inside the elevator and pushed a button. Just as the doors began to close, Blair slipped her hand in-between them and they opened again. Serena looked up from where she had been studying her nails, and her expression was shocked.

"Blair!"

"I followed you, S. Where are we?"

Serena's expression left no doubt in Blair's mind that they were headed to the speakeasy, and she scowled fiercely at Serena. "Why can't you get it through your blonde head, that we should not be here! We could get in serious trouble with the police!"

But the doors of the elevator had closed, and it was going down. Blair saw Serena had pressed an unlit button marked 'B', presumably for basement.

Blair dreaded what she would find, and when the elevator doors opened she stepped out into the basement with the feeling of someone who had just been delivered to the devil's lair.

**A/N**

**I actually did research for this, and I really hope I got everything right!**

**Huge thank you to Guardian Izz, who inspired me to put some effort into my stories, instead of just writing as I go! **

**Please review!**

**XOXO**

**Lissa**


	2. Chuck Bass

Another new story idea, again a trial, so let me know what you think!

**Story: **Prohibition and a gangster named Bass

**Author: ** LadyLissaLight

**Summary**: Picture the roaring 20's. The prohibition act has just come in, and Chuck Bass, bootlegger and sometimes-gangster, has never been more popular. Except, of course, with Miss Blair Waldorf.

She stared. It was the basement, certainly, but the walls had been done up in the most lavish decorations. Deep red and purple velvet, gold draping, and low lit lamps adorned the walls, making the atmosphere dark but exciting. The room was packed with many figures swaying to music that was being played by a band that Blair could see at the other end of the room, on a slightly raised platform. There were many couples doing things that Blair chose not to look at, and instead averted her eyes, blushing. She was confused. It looked like a normal party. A slightly wild and out-of-control and scandalous party, but certainly not a speakeasy.

Then, in the corner of the room, a long table was against the wall, and behind it stood figures, handing paper bags to anyone that approached. Blair's eyes narrowed on the paper bags, and she realised this is what hid the alcohol.

Serena, still beside her, was taking it all in too, and smiling in excitement. "Serena!" she hissed, "we have to get out of here!"

Serena ignored her and made her way into the crowd of dancing figures. Blair darted out to follow her, trying not to touch anyone else. She followed her friend though the crowd, figuring that she would at least make sure Serena consumed no alcohol.

Serena approached the table in the corner, and Blair tried to pull her away. The blonde shook her off and stepped forward. There were three figures behind the table, two men and a woman. The woman had dark hair and grey eyes, and her gaze was sinful and calculating. The first man was blonde-ish with a sultry smile that made Blair shudder in horror.

The third man was the one Serena was trying desperately to catch the attention of. Blair stared at her friend, who was standing upright, and sticking her breasts out in a most undignified manner. Blair also noted that Serena had adjusted the straps of her dress so that it hung lower and drew eyes towards her chest. Blair was disgusted with her friend.

She turned her eyes towards the man her friend was so desperate for, and found herself shocked. He was the prince from her dream. Not the same prince, but he had the same features she always dreamed about. He was tall, and his cheekbones were high, speaking of elegance and wealth. H e had dark hair and alabaster skin, and his lips were full and soft. His eyes suddenly swept sideways and landed on her, and she drew breath. They were slanting, and so dark that she would have thought he had no soul. They drew her in, and she could not look away.

Then he glanced away, carelessly, and she found herself staring at the ground in shock. Ignoring the blonde man, who was leering at her, she turned to look at Serena, and found herself once again in disgusted shock.

The dark prince, as she now thought of him of, was now standing next to Serena, and openly fondling her breasts, while tracing slow circles with his lips and tongue on her neck. Serena, for her part, had her head tilted backwards and her eyes closed. Then the man let go of her, and walked back over to the table, where he proceeded to have a conversation with the dark haired girl.

Blair was feeling disgusted and sick by now, and turned to leave, when a paper bag was shoved in her face by someone. She held it, unsure of what to do, when a slinking, silky voice whispered in her ear, "you're supposed to drink darling. That's what your here for." Blair's neck erupted in Goosebumps at the voice, and she turned to see the dark prince.

"No thank you," she said boldly, ignoring his alluring eyes. "I only came here to make sure my friend," she gestured to Serena, "did not partake in anything that would cause harm to her reputation. However, as I doubt I can stop her, I was about to leave." She handed him the paper bag, and turned to go.

The soulless eyes flamed, and he whispered again, "I suggest you drink darling, or you might be thought of as a spy, and shot. You can never trust that someone isn't an informant." He was looking at her dangerously, and she wondered who he was. "Might I enquire as to your name?" she asked suspiciously.

He returned her suspicious look, "either you're playing innocent, and trying to get me to reveal who I am so you can report me," he said slowly, in his silken voice, "or you really are clueless. But," he gave her a once over and his lips curved into a smirk that made her heart pound, "I think your incapable of being a spy. In which case, you may know."

She waited for him, but he simply smirked at her. She was starting to feel quite irritated, and was about to say something sharp, when he said, "I'm Chuck Bass."

She felt faint. Chuck Bass. The swindler, bootlegger, and sometimes gangster Chuck Bass. He had the worst reputation in all of New York.

Rumour had it he ran a ring of underground clubs and speakeasies, and he ran a prostitution ring. He was definitely bad news. And Blair had been talking to him for the past few minutes. She felt horror rise within her, and the urge to run away strengthened.

But instead of running, she asked, "Do you know Al Capone?"

To her surprise, Chuck's lip curled. "Al Capone." He said the name like it was a dirty word. "Of course I know him. But you oughtn't believe the rumours that we're comrades, because I would never consort with someone who comes from _Brooklyn_." Blair was surprised. If anyone else had said that, she would have laughed and agreed whole heartedly.

"Well, I'd say it has been a pleasure meeting you, but really, it hasn't." She said. "Goodnight, Mr Bass." She turned to go, but once again, his voice caught her.

"It's polite to tell a gentleman your name in return for his," he said slyly.

She thought to herself. Of course she wasn't going to give him her real name, only someone as stupid as Serena would do that. She just hoped Serena hadn't actually gone and done just that.

"Audrey... Hepburn." She said, "now if you'll excuse me, I have better things to do than consort with lowlifes such as you." She added nastily.

She made her way over to Serena, who was standing in the same position as before, and grabbed her arm. "You're coming with me," she hissed, and forced her friend into the elevator.

The two returned to the surface, and Blair hurried them down the street, scared that an unsavoury character would come along and accost the two. They arrived back at Blair's brownstone, and she couldn't help but be a little disappointed that neither her mother, nor her stepfather had arrived home to see her.

Serena wasn't speaking to Blair, but the brunette climbed into her bed, and waited for the blonde to climb in next to her, which she eventually did.

"Blair, I know you probably think I'm a complete whore now, but I just... I've never felt this way about anyone before. I really like Chuck, and this is the only way I can get him to even come near me. Unless you have something physical to offer, he doesn't even bother to say hello, much less care who you are."

Blair was silent. Chuck Bass had approached her, spoken to her, and asked her name, and she had tried to not catch his attention.

**And so they meet!**

**XOXO**

**Lissa**


	3. Dreams

**Story: **Prohibition and a gangster named Bass

**Author: ** LadyLissaLight

**Summary**: Picture the roaring 20's. The prohibition act has just come in, and Chuck Bass, bootlegger and sometimes-gangster, has never been more popular. Except, of course, with Miss Blair Waldorf.

**I know you guys wanted some Chuck POV, but right now I'm slightly stumped for Chuck's view of things. I shall try and get some in next chapter though, promise. **

Blair turned her head restlessly in her sleep, almost kicking Serena as she stretched. She was dreaming again, and this time, her dark prince's features were all too familiar.

Chuck Bass.

He was dark, and glorious, and magnificent. He spoke of danger, and seduction, and all the things that Blair knew as bad, but she was drawn to him. She wanted nothing more than to be in his arms... and revel in his kiss...

Blair woke with a start, her heart pounding. Serena's form lay next to her, still asleep, but Blair knew she would not be able to shut her eyes again, for fear of slipping back into the dream about Chuck.

Chuck Bass, she thought furiously. He was a pervert, and a creep. He was most definitely not someone to star in her dreams, to be her prince. And yet, when he had looked at her, she had felt something strange, a lurch in her stomach that she had never felt before.

She chose to ignore the dream, and hope that he would not become a regular feature of her dreams.

She shook Serena awake, and the blonde yawned. "Blair," she said reproachfully, "I was having a good dream. It was about Chuck Bass," she giggled, and Blair's heart dropped.

"Serena," she protested, "I do not wish to hear about your scandalous dreams, especially if they are with that Basstard."

"Fine," Serena huffed. "I have to be getting home. Mother will be worried."

They both knew this was a lie, Serena's mother was always out with her boyfriend, or boyfriends, and she never gave a second thought to her teenage daughter, or Serena's younger brother, Eric. But if Serena wanted to leave, that was fine.

Blair kissed her friends cheek, and then the taller girl departed.

Blair called Dorota, and the maid hurried in with her mistress's breakfast of porridge with honey. Blair ate, while reading the society pages. She almost spit out a mouthful of porridge, as she looked at the 'Lost and Found' pages.

It read:

**Lost:** One female, brunette, about 5'4, brown eyes. Name of Audrey Hepburn. If found, please come to the address of..."

There was the address of the building Blair and Serena had attended the night before.

Blair could not believe that there was someone advertising for a _person _in the Lost and Found section, or that the paper had published it. Unless they had been paid too f course, and it was rumoured that Chuck Bass was a billionaire.

She couldn't believe it. Why was Chuck looking for her? Maybe he wanted to kill her.

Blair felt frightened, but strangely, pleased. She had clearly made an impression on him if he was looking for her. Then she felt annoyed with herself for caring. He probably wanted to do the same thing he had done to Serena.

He probably wanted to take her virtue. She shuddered at the thought.

While some girls may not have cared about this, Blair was not one of them. She did not believe in any of this 'new age' nonsense, of wearing clothes that were more revealing. She was not a whore; she would dress appropriately, and behave according to her station. This Chuck would only do her reputation harm.

She decided to ignore the column, like she had the dream, and went about her normal day, calling Dorota back in to help her dress, and then walking down fifth avenue.

In Henri Bendel, she was having a dress fitting for a delightful salmon coloured dress, when she spotted two of her oldest friends, as well as admirers, Katia and Isabelle, to their friends, Kati and Iz.

"Kati, Iz!" She greeted, and the two rushed over, and they kissed each other's cheeks. "Blair! Are you attending the Carmichaels party tonight?" Asked Iz eagerly.

"Of course," Blair smiled in a superior fashion. "Although Daniela herself neglected to invite me, her social-climbing mother made sure I got an invitation." Blair rolled her eyes, and the two girls tittered excitedly.

"What did you do this time, Blair?" Kati giggled.

Blair was notorious for being rude to the other, lesser, girls of their age, and she undoubtedly made them jealous and angry. The girls themselves all hated Blair, yet feared and admired her, but their mothers, knowing that Blair was a Waldorf, and therefore a Queen in their society, made sure that she was invited to all the party's.

"Oh, I just informed her, that I had seen her purchasing the dress that she told everyone she bought at Lord and Taylor, at Gap," She sneered at the name of the lesser, non couture store.

Kati and Iz gasped theatrically, "Like, oh my god!" whispered Kati.

Blair privately thought that these girls were extremely annoying, but she had to keep her minions close, so she nodded in agreement.

"Disgusting."

"So, what about the rumours we heard about Serena at the _speakeasy_?" Iz whispered conspiratorially.

"Oh! Totally false," Blair said pretending to be shocked. "I was with her that night, and we stayed in and had Nathaniel over."

"Oooh Nathaniel," the girls giggled together, and Blair longed to be away from them. "Surely you'll marry him, Blair? He _is_ a Van Der Bilt."

"Don't be silly," Blair snorted, rudely. "Nathaniel and I are merely the best of friends. If he was to marry anyone, it would be Serena. Now, if you ladies will excuse me, I have a dress fitting. I shall see you tonight."

She strode briskly away from the two other girls, who resumed gossiping.

XXXXXX

The Carmichaels were UES middle class. Wealthier than the average person, but poorer than the top of society, like the Waldorfs.

Their house was reasonably large, and when Blair arrived, the party was already in full swing.

Dressed in a red dress, with a silver necklace with black feathers, and a silver headband, Blair immediately commandeered the attention of most of the room as she entered. She gave the room a cool smile, and went t find Serena.

The blonde was chatting with Hazel and Nate, and when Blair joined them, she acted less than happy to see her. Blair quickly pulled Serena over to the side of the room, "S! Stop acting like I've done something wrong." Blair glared at her friend, who rolled her eyes.

"It's not my fault you're jealous," Serena mumbled.

"Jealous?" Blair almost laughed. "I'm Blair Waldorf, what would I possibly be jealous of?"

"That I discovered the speakeasy and you didn't! That Nate took me and not you! That I'm more exciting and you're just boring Blair," Serena declared.

Blair felt the words like a blow to the head. She turned away from Serena, who was, she decided, no longer her best friend, and walked away.

She had barely left the room, when she ran into someone. Looking up, she couldn't believe her eyes.

She surely must be dreaming. Chuck Bass could not possibly be at this party. Why were there not police everywhere?

"Miss Hepburn," his voice was pleasantly surprised, but his eyes showed no surprise at seeing her at all.

"What are you doing here!" she exclaimed. "How did you get an invitation?"

"I have my ways," he said smoothly.

"Well, have a nice evening Mr Bass," she said loudly, but no one heard her. She tried to hurry past him, but he caught her arm.

"You're not leaving me just yet, Miss Hepburn. I worked very hard to find you again," He smirked.

"And why would you do that?" she hissed. "I am a respectable girl, and I will not have m reputation sullied by you. Now, leave me be. I am not one of your prostitutes or whores."

Her voice was cold, but he did not look dis-heartened. If anything, his smirk grew broader. "You have a very sharp tongue, Miss. I would quite enjoy talking with you," His voice held a hint of something seductive, and his appraisal of her body left little doubt in her mind that he did not mean 'talk'.

"I would not enjoy talking with you at all, Mr Bass," she snapped. "As I fear that your intellect and your speech would be quite poor, as I doubt any of your conversations actually involve talking."

She spun around, and flounced off, turning back once to see his surprised expression.

**A/N**

**So, I realise that the store 'Gap' would probably not exist in 1920, but I needed a lower class but still reasonably priced store, so I used that.**

**Review please!**

**XOXO**

**Lissa**


	4. Blair Waldorf

**Story: **Prohibition and a gangster named Bass

**Author: **LadyLissaLight

**Summary**: Picture the roaring 20's. The prohibition act has just come in, and Chuck Bass, bootlegger and sometimes-gangster, has never been more popular. Except, of course, with Miss Blair Waldorf.

**And here we finally have some Chuck POV! **

Blair left the Carmichaels party confused, upset, and frustrated. Serena had been so horrible to her, and Serena was usually the sweetest person on the planet. And how had Chuck Bass managed to get himself into the party! It made no sense! He should have been arrested as soon as he walked through the door!

And what made matters worse, he seemed to be following her! First the advertisement in the paper, now this. She was extremely glad that she had given him a fake name or she had no doubt that she would have been kidnapped, or something worse, by now. But why was he interested in her? Was it because she had refused to drink at the speakeasy? Or because he had told her his name and suspected her of being a spy?

Blair huffed as she thought about him, walking back to her brownstone. All her problems stemmed from Chuck Bass. He was a problem. He'd made Serena into some disreputable groupie, now haunted Blair's dreams, and was looking for her!

What was she going to do?

XXXXXX

Chuck Bass stared after the retreating from of 'Audrey Hepburn', surprised. He hadn't met a girl like her before, she was a complete oddity.

In Chuck's experience, girls either wanted to sleep with him, or were afraid of him. This one was neither. When he had first laid eyes on her, he had thought she was beautiful. The porcelain skin, the red lips, and the way she acted, like she was totally pure and untouched. Chuck wasn't used to girls like that. Then he had spoken to her, and she hadn't acted pure or afraid of him, she had been rude and hadn't even seemed frightened when he told her that he was Chuck Bass.

And she definitely hadn't acted the way her blonde friend had. The blonde was more the type Chuck was used to. Girl's that just wanted it, or wanted him, and would do anything for his attention. This girl, however, didn't seem to want his attention.

She fitted into neither category, and Chuck was confused.

Her name wasn't really Audrey Hepburn of course, she had taken too long before replying for it to be real, and her eyes hadn't matched her mouth, as they had the rest of the time he had spoken to her.

The way she had spoken, as if he was beneath her, and not a well-known gangster that could easily shoot her, made him fascinated. He had to find out who she was.

He had placed the advertisement in the paper to scare her, and for his own amusement, not because he actually expected to find her. But that night he actually had, to his pleasure.

She had looked gorgeous, beautiful, definitely worth setting his sights on. But her tongue was so sharp that he found her wit just as enticing as her looks.

Now, as he watched her go, he smirked to himself. Then a hand stroked his shoulder casually and he turned to see the girl who was friends with 'Audrey'.

This one, he thought, was clearly desperate for his attention. Since he was too distracted by her friend at the moment, he wasn't going to bother with her.

She gave him a coy smile, then, just as he was planning on shrugging off her hand and leaving. "Why were you talking with Blair?" she asked, batting her eyelashes.

"Who?" he asked suddenly, hardly daring to hope that her stupid friend would give away her name.

"Blair" the blonde repeated. "My friend. You wouldn't like her. She's ever so boring and annoying and no fun at all. I mean, she made me leave the speakeasy and everything. What a priss," Serena rolled her eyes and smiled at Chuck again, clearly thinking that he would agree.

"Blair," he savoured the name as he contemplated her, "the brunette?"

"Yeah," said the girl, "but more importantly, "I'm Serena." She smiled again.

"Well Serena, I have no interest in talking with you," he said, rudely, turning to leave.

"Well I have no interest in talking with you either," she smiled seductively and stepped closer to him.

"Maybe another time," he smirked at her, before untangling himself and quickly walking away.

Outside the party, he hoped to catch a glimpse of Blair, but she was nowhere to be seen.

But now he knew her name. He smirked to himself in satisfaction.

Returning to Victrola, the underground rooms where he held speakeasies every night, he lounged on a couch and closed his eyes, till a voice made him jump.

"Well, well, Chucky, home early? I thought you were going to be out all night..." He opened his eyes to see the dark haired girl standing in front of him.

Her eyes were wicked with malice, and she was scantily dressed. "I was, G," he yawned, "but my prey got away from me for the moment. Am I interrupting something?"

"I just have a few boys out the back," she smiled.

Chuck smirked, "doing what?"

She shrugged, "a bit of this, a bit of that... care to join?"

"No thank you, G. But you have fun with your toys," she smirked at his words.

"Oh I will... Want me to send out for some of your whores?" She mocked, knowing that Chuck had slept with all of them already, and he never slept with the same girl twice.

"Funny, G. Where's Carter?"

"He left with a few girls and a few bottles about an hour ago."

"Wonderful. I'm in need of sleep," he mumbled. "You can go now."

"As his majesty commands" she bowed, and left the room.

XXXXXX

She was dressed in only her slip, and his breath was hot on her neck as he kissed her feverishly. She moaned his name, "Chuck..."

"Miss Blair!"

Blair woke with a start to see a shocked looking Dorota bending over her. Flushing, Blair glared at Dorota, "Do you often spy on me whilst I am sleeping! Get out!"

The maid retreated from the room, muttering in Polish. Blair sank back down then realised with horror what she had been dreaming about. Chuck.

It had been two weeks since she had seen him at the Carmichaels, and she had dreamed about him every night. It was getting worse, the dreams were getting more scandalous, and Blair didn't know what to do.

She sat up, ignored the breakfast next to her bed, and got dressed.

She walked down the road, intending to head towards the shops and buy some clothes to distract her from her dark haired nightmare, when she ran into a man. He was blonde and looked slightly familiar. "Excuse me miss," he flashed her smile.

He was carrying a package and smelled... like alcohol. He was the man from the speakeasy!

She drew back immediately and scowled at him, before turning around.

"What's your name?" he said suddenly.

"Audrey Hepburn," she told him confidently, making use of her made-up name.

Unfortunately, he grinned at her most frighteningly, "Ah, Miss Hepburn is it? You'll have to come with me. The boss has been looking for you."

He took her arm, and she wrenched it away, "I will not go anywhere with you," she said coldly.

He linked his arm through hers again, "Yes you will, my love," he smiled at another person passing.

"Fine," Blair snapped. "Mr Bass doesn't scare me anyway."

The man chuckled.

XXXXXX

The girl smiled at Chuck as she sinuously climbed on top of him and pushed him down onto the bed, her naked body lying flat against his. He smirked at her and reached around to stroke the inside of her legs, when Carter knocked on the door. "I'm busy," Chuck called, and the girl smiled again.

"You won't be too busy to see _her_, Bass," Carter's voice was amused.

Chuck sat up, pushing the girl off him, and pulled on his purple velvet robe. She pouted, "You can go," said Chuck, already bored with her.

He opened the door to see Carter standing there. The blonde eyed his friend's attire, and smirked.

"I see you were busy, how many?"

"Only one, but I heard she needed taming," the two exchanged knowing looks.

"Where's Blair?" Chuck asked.

"In G's room. I happened to accidentally run into her on the street. I apologised, and then she glared at me and tried to run away. I asked her name, she said 'Audrey Hepburn' "he grinned. "Then I told her I'd have to take her to see you, and she said, 'I'm not scared of Mr. Bass'," he mimicked a girl's voice, and the two chuckled.

Chuck walked into Georgina's room to see Blair standing next to the bed, looking quite out of place in the less than clean room. Georgina wasn't one for tidiness.

"Mr Bass, whatever obsession you have with me, get rid of it, and release me," she said furiously as soon as he entered the room.

"Miss Hepburn... or should I call you Blair?" he crept forward and whispered in her ear, enjoying her slight intake of breath.

"Who told you?" She still didn't seem frightened. He liked that.

"Your ditzy friend, Samantha... Selena...?"

"Serena," Blair snapped. "And she isn't my friend. Thanks to you."

"What?" Chuck said, now confused.

"Nothing," she returned to glaring at him in silence. He stared at her for a few more seconds, taking in her carefully styled curls and the headband she had placed neatly in them, her large doe eyes, and her plump lips. Could any girl be more perfect? He wondered. "Stop staring at me like I'm one of your whores," she said, irritated.

He laughed, "I'm quite sorry to disappoint you, but I never really look at my whores, so you can't compare yourself to them. I prefer to feel," he smirked and she cast him a withering glance.

"Your jokes are crude, and if you were a gentleman then you would not make them in front of a lady, particularly one such as me."

He laughed. She was witty, and beautiful. He couldn't wait to have sex with her. "Well, Miss...? You really should tell me your last name; it's fairly obvious I'm not a gentleman."

"Clearly, as you don't dress like one. Do you often wander around your house wearing a robe and naught else?"

"Would you like to see?" He smirked as she flushed. "How innocent you are, Blair," he stroked her name as it came out of his mouth.

XXXXXX

Chuck's voice was extremely smooth, yet husky. Blair flushed at the way he caressed her name, and she couldn't help her eyes from straying to the open part of his robe, that revealed some of his chest.

"Mr Bass, you will tell me what you want with me," she said, her voice coming out quite firm, to her relief.

"Do you want the gentleman-like version, or the crude version?" his smirk deepened, and Blair couldn't deny how attractive it was.

"The crude version," she said, "because I suspect you would lie to me if I asked otherwise."

"I never lie," he told her. "I find no need to."

"Why?" she asked him curiously. He shrugged.

"Do you often lie? Audrey?" He was mocking her, she was sure.

"I am a lady of society, of course I lie," she told him. "I lie when I say I like the dress Kati is wearing, or when I say no, I don't wish to discuss politics with the men and that I'd much prefer to do some needlepoint."

He stared at her, and she realised that she had said something totally pointless. "Well," she prompted. "Tell me what you want with me, so I can refuse you, and you can let me go."

He chuckled, and she found that his smile was rather nice. Not that she was looking. "Well, you wanted it the crude way, Blair... So I will well you. I want to have sex with you," he said simply.

"Mr Bass, you are heinous, and disgusting." She told him disdainfully, although her heart skipped a little, with fear and something else. Maybe he would force himself on her? She should have gone to the Police when she had had the chance.

But Chuck Bass, she thought, didn't seem the type. Even though he was Chuck Bass.

He was still smirking. "You may not want it now, but eventually you'll give in. I shall wear you down until you are mine," he whispered huskily, and Blair felt goose bumps erupt along her arm.

"I will never be yours," she said coldly. "I am not a whore, Mr Bass, and to even suggest I would do such a thing with the likes of you, is insulting." She ignored the fact that she was dreaming about it.

"The likes of me?" his eyes flashed dangerously. "Don't think to put yourself above me, because you have no idea."

"Let me go Mr Bass. Unless you plan to take my by force, we're done here." She said dismissively.

He was a centimetre away from her in an instant, her breath was uneven and he stared into her eyes. "And if I do?" he said, into her ear.

She felt shudders run along her body. "I don't think, Mr Bass," she began, choosing her words carefully, "that you are that type of man."

He stared at her for another second before grabbing her waist, hard, and pulling her towards him before crushing his mouth onto hers. It was a hard kiss, and she couldn't breathe. His mouth was firm on hers and it was so, so hot. Then he let her go and she gasped.

"You can go now, Blair. If you tell me your last name," he said, opening the door for her.

"Waldorf," she couldn't help herself, before she fled the building.

**Review, please!**

**XOXO**

**Lissa**


	5. None of your business

**Story: **Prohibition and a gangster named Bass

**Author: **LadyLissaLight

**Summary**: Picture the roaring 20's. The prohibition act has just come in, and Chuck Bass, bootlegger and sometimes-gangster, has never been more popular. Except, of course, with Miss Blair Waldorf.

Waldorf. Of course, he thought almost bitterly.

The Waldorf's were old money. They ran in certain circles that the rest of society found it near impossible to get into.

He should have guessed she was one, or at least something of the sort. The way she dressed, and the way she seemed to look down on everything and everyone as if it was lower than her, bespoke importance, and class.

When she had told him, almost shaking, that he wasn't the type of man to force himself on her, he had been angry. How dare she presume things about his character when they had met a mere three times? Or more accurately, he thought to himself, how did she understand him that well already? Nobody would even dare to think that Chuck Bass wasn't an evil drug lord who shot at will and forced himself upon any woman he wanted.

But Miss Waldorf has whispered that he wouldn't do that. Why did she think that? What impression had he given her?

At least she had seemed afraid. Or was she? Maybe she was shaking from something else.

When he had kissed her he had felt something he had never felt before. Although her kiss was obviously inexperienced, in fact he suspected it was her first; there had been something about it that had made his blood boil. No whore, socialite, or any other girl he had ever slept with had made him feel like that. It had been all he could do to stop, and not throw her down on the bed and take her.

But she was a Waldorf. And that complicated things. He should give up on her. Find another ravishing brunette with scorching eyes and tempting lips, and forget Blair Waldorf.

But he couldn't.

XXXXXX

Her lips burned as she thought of him. How dare he? She thought hotly. How dare he kiss her like that? And then demand her last name when she was clearly overwhelmed. She ignored the fact that she had liked it. More than liked it. When he had kissed her, it had been better than any of her dreams, and she found herself reliving it over and over, and when she should be listening to those around her, daydreaming about Chuck Bass.

She hadn't spoken to Serena since the Carmichaels party, and she wasn't planning to. That is, she wasn't planning to until Nate hurried into her room, accompanied by a flustered Dorota.

"Blair!" Nate announced, without knocking, at the same time as Dorota exclaimed, "Mr Nate is here to see you!"

"Nate!" Blair looked up from her novel and gave him a scandalised look, "Don't come into my bedroom!"

Her friend seemed to remember where he was, and hastily retreated a few steps till he was in the hallway.

"What are you doing here?" she asked curiously, climbing off her bed and stepping into the hallway to join him.

"It's Serena," he blurted. "She's gone off with... I don't know his name, but he works with Chuck!"

Blair knew immediately that Nate was talking about the blonde man. Carter. "You mean Carter? Why is she with him?" she demanded.

"I don't know! I just took her with me to visit Chuck, since we are friends you know, and Chuck wasn't there, but Carter started hitting on S, and then she went somewhere with him!"

"And you let her!" Blair exclaimed, hurrying down the stairs with Nate behind her. "Dorota, I'm going out," she briefly called, before herding Nate out the door.

"Ok, where did you last see them?" ashe demanded.

"Victorla..." Nate looked helpless.

"Right, we'll start there." The two walked briskly towards the hotel under which Victrola was hidden.

"Blair," Nate paused. "How do you know where Victrola is?"

Blair cursed internally. She had wanted to keep her reputation intact. "I had to follow Serena one night and get her home," she said truthfully. "I am so disappointed in you Nate. Consorting with gangsters."

"Well, Chuck and I were friends before-" he broke off, looking shifty.

"What?" Blair narrowed her eyes at him as they reached the building and stepped inside.

"Nothing," Nate said firmly, pushing the elevator button.

Hey arrived in the underground room, empty at the moment, and Nate led Blair towards the door that Carter had taken her through the last time.

They stepped through the door into the 'common room' of the mobsters. A brunette girl was laying on a sofa, flipping through a magazine. As they came in, she looked up, and a smirk appeared on her pretty but malicious face.

"Well, well. Chucky's girl and Chucky's BFF. What are you doing here?"

"I am not Chuck's girl!" Blair protested hotly, but Nate shot her a look.

"We're looking for Serena..." at the girl's blank look, he continued, "she's blonde... she left with that... Carter guy."

"Ah," her expression cleared and her grey eyes sparkled with something Blair didn't like. "Her and Carter went... somewhere. I don't think you want to find them, if you get my drift," she shot a wink at them.

"How dare you!" Blair snapped. "Serena would never do... do that!" she protested.

"Well she seemed pretty into Carter," the girl smirked.

"But that makes no sense. She's like, in love with Chuck," Blair frowned to herself.

"Talking about me... Miss Waldorf?" Blair's heart skipped a beat as Chuck emerged from a room and leaned casually against the sofa, cigarette in mouth, glass of something that looked alcoholic in his hand. His hair was carefully parted and oiled into a perfect style, and he wore, to her surprise, a coral suit with a grey shirt underneath.

His eyes took in her appearance, pausing in certain places that made her blush. Her gaze was drawn to his lips, the same lips that had kissed her so wildly. She pushed the memory away and glared at him. "Where is Serena? What has Carter done with her?"

"Carter," he drawled, "has done nothing with her. Hello Nathaniel. What are you doing with her?" he added.

"Oh... I didn't know you two knew each other," Nate looked confused. "Blair's my..."

"Fiancée," Blair interjected. "Or will be, soon enough."

Nate glanced at her in confusion, but nodded at Chuck. Blair felt a rush of gratitude for her best friend.

Chuck's eyes flashed, and for a second, she thought he looked angry. But a moment later he was calm, and composed. "I see." He was looking at her. She stared expressionlessly back. "I suppose congratulations are in order Nathaniel," he smirked. "As for Serena... She and Carter are busy."

"I demand you take me to her!" Blair snapped.

Something flickered in Chuck's eyes, before he nodded. "Very well, Blair," he spoke her name softly, like he was stroking it.

He led her towards the elevator, and she looked back at Nate. "Are you coming?" she called.

"Ah, I think i'll stay here," he returned, with a glance at the brunette girl, who smiled wickedly.

Chuck pressed the button for the top floor of the hotel, "Why are we going up there?" Blair objected. "We have to find Serena."

"And this is where we shall find her," Chuck replied, sounding bored.

There was a sudden lurch, and Blair almost fell against Chuck. The lights above them flickered momentarily, before the elevator came to a halt.

"What is it?" Blair cried.

"There must be something wrong with the elevator. They'll sort it out soon enough," He shot her a smirk before sitting down on the floor.

"Ugh. Wonderful. Honestly, the idiot that owns this building will be hearing from me!" She frowned, before emulating Chuck and sitting.

"I'll take it under consideration," a smirk was playing around the corners of Chuck's mouth as he spoke, but his eyes revealed something else.

"What...?" She asked in surprise.

"How did you think I managed to set Victrola up in the basement?" he looked extremely amused.

"_You_ own this building...?" she asked, hardly daring to believe it.

"I do," he replied curtly, not elaborating.

"But, but..." she stumbled for words. How could Mr Bass own a building? He was a gangster, a bootlegger? Only the most respectable and upper class gentleman owned building such as there. And a hotel too! It was too much to take in.

"Miss Waldorf, are you possibly lost for words?" he asked sardonically, but his eyes twinkled.

"I do not understand," she said finally.

"And nor do you need to," he replied. "For it is none of your business."

There was another lurch and the elevator rose again. Chuck climbed to his feet before offering his hand to Blair. She took it, and felt its warmth, and smoothness. It fit perfectly with hers, and somehow she didn't want to let go.

Then, as the elevator doors opened, she heard a giggle. A giggle that sounded very much like Serena's.

**Review.**

**XOXO**

**Lissa**


	6. PLEASE READ

**OK, guys.**

**I have important news. **

**I've just started year twelve (Senior Year) and I don't have time to be writing all my fics as well as the home-work and assignments I have to do.**

**OI have the time to write two stories, but not the amount I have going. One of these two is going to be my Draco and Hermione story. **

**So, I've created a Poll on my profile, and I'd like you all to vote as to which ONE GG story you think I should focus on. Please, please, PLEASE, vote.**

**XOXO**

**Lissa**


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